Antistatic additives and their preparation



United States Patent 3,161,486 ANTESTATIQJ ADDlTlVES AND THEIRPREPARATIQN Dilworth T. Rogers, Summit, and John P. McDermoti,

Springfield, N.J., assignors to Esso Research and Engineering Company, acorporation of Delaware No Drawing. Filed May 18, 1961, Ser. No. 110,898'17 Claims. (C1. 44-51) The instant invention concerns a process fortreating antistatic additives to enhance their ability to promoteelectrical conductivity. In particular, this invention relates to amethod of concentrating the colloidal fractions of antistatic additivesin a liquid disperse system to obtain the more active antistaticfractions and compositions containing these fractions. This applicationis a continuationin-part of Serial No. 784,087, filed December 31, 1958,now Patent No. 2,992,909, and Serial No. 9,690, filed February 19, 1960,now Patent No. 3,084,038.

The generation, accumulation, and retention of excessive electricalcharges during the processing, handling, storage, and transportation ofcombustible organic fluids have been a potential and suspected source ofmany explosions and fires. Particularly hazardous in this respect arecombustible organic liquids boiling between 75 F. and 750 F., such ashydrocarbon oils and petroleum distillate fuels and organic volatileliquids preferably containing not more than an average of 12 carbonatoms per molecule, since with these liquids the danger of ignition orexplosion occurring as a result of electrical charges is particularlygreat. Hazardous operations are not restricted to volatile liquids, butmay also occur when, for example, a fluid product having a tendency togenerate, accumulate, or store electrical charges is pumped ordischarged into a tank or storage area containing a combustile vapor. Inorder to reduce the hazards of ignition and explosions, variousantistatic additives have been incorporated in fluid products andparticularly in these combustible organic liquids in minor amountssuflicient to increase the electrical conductivity of these liquidsusually to greater than 1x10 mhos per centimeter. These additives arenormally employed in minor amounts or in concentrations of from 1.0 toabout 0.00001%- by weight and preferably from about 0.1 or even 0.05 to0.000l% by weight.

Some of the additives suggested to increase the electrical conductivitywhen employed in amounts suflicient to promote electrical conductivityin many cases adversely affect the Water tolerance, thermal stabilityand other characteristic properties of the organic liquid, such asaviation turbojet fuels in which they are incorporated. Additionally,certain ash-forming metallic additives are particularly disadvantageouswhen utilized in certain fuels where the amount of ash formation isrequired to be at an absolute minimum, e.g., in the operation of aturbojet engine. It is, therefore, an object of this invention todescribe a process of treating antistatic additives to enhance theirelectrical conductivity effects when incorporated in organic-liquids. Afurther object is to provide a method of concentrating the more activecolloidal fraction of antistatic additives for subsequent incorporationin hydrocarbon oils. An additional object is to disclose a method ofsegregating the active fraction of metallic antistatic additives so asto reduce the amount of additive required for antistatic protection injet engine fuels and thus reduce ash formation during the operation ofjet engines on this fuel. I

It has been discovered that the colloidal fraction of antimotingelectrical conductivity than the noncolloidal fraction of theseadditives. When a colloidal system containing a disperse phase of anantistatic additive in a dispersion 8,161,486 Patented Dec. 15, 1964tion or all of the colloidal fraction, the more antistaticv activeportion of the additive may be obtained. The colloidal fraction obtainedmay then be employed at a lower concentration level in combustibleorganic liquids or hydrocarbon oils to yield the desired electricalconductivity previously only obtained by higher concentrations of thetotal colloidal and noncolloidal fractions. The numerous advantages andbeneficial results of treating combustible organic liquids orconcentrates containing antistatic additives, or combinations thereofwith other ingredients, or the antistatic additives themselves, toobtain the active colloidal fraction or to increase the concentrationlevel of the active colloidal fraction above that of the originalconcentration is apparent to those skilled in the art.

The additives which may be dialyzed or otherwise treated to increase theconcentration of the colloidal fraction and obtain enhanced electricalconductivity characteristics are impossible to divide on the basis ofindividual compounds, generic groups and substances, since thedistinctions between colloidal substances and crystalloidal substancesare not rigid (Textbook of Physical Chemistry, 2nd edition, Glasstone,page 1231). The colloidal systems with which the present invention isconcerned include those systems wherein the dispersion medium is anorganic liquid and wherein the antistatic additive comprises anoncolloidal and a colloidal fraction or forms a colloidal and anoncolloidal fraction in said liquid. These colloidal fractions are ingeneral made up of submicroscopic particles having an averageparticle'diameter of less than 1 micron, for example, average diametersranging between 0.001 micron and 1 micron, i.e., 10- and 10"centimeters, and preferably between 0.2 micron and 0.005 micron. Ingeneral, the nature of the particular substance employed is not ofprimary importance, for example, whether metallic or nonmetallic.importance with metal or ash-forming compounds since concentration ofthe active portion will reduce the amount of possible ash deposits injet engine operation.

Suitable additives which benefit from the present discovery include: theorganic soaps of polyvalent metals, such as the fatty acid metals; GroupVI metals like chromium; Group III metals like aluminum; transitionmetals like cobalt, iron, nickel, and the like; the antistatic first andsecond additives disclosed in British Patent 749,898, published June 6,1956, for example, the metal salts of alkylated salicyclic acids, suchas chromic diiso'p ropyl salicylate, and combinations thereof.Particularly enhanced by the complexes disclosed in the parentapplications, such as the chromium, aluminum, iron, cobalt, nickelcomplexes and the like. These metal complexes are prepared by reactingthe'aliphatic C C monocarboxylic acid metal salt, e.g., chromiumacetate, with a high molecular weight monocarboxylic acid, e.g., oleicacid, or with an alkyl phenol sulfide, e.g.,'dodecyl phenol sulfide, toyield complexes which form a collidal system in organic liquids,

e.g., isooctane.

The method discovered by the applicants is not restricted to metallicadditive compounds, but includes Of course, this method will be of.

salts of the alkali or alkaline earth nonmetallic antistatic compoundssuch as the amine salts of fatty acids, like guanidine tallate, asdescribed in US. application 16,966, filed March 23, 1960, now PatentNo. 3,062,630; alkyl hydroxy aromatic sulfide; alkylated phenolsulfides, like dodecyl phenol sulfide; quaternary ammonium compounds,like tetraaliphatic quaternary ammonium additives like dimethyldialkylammonium chlorides, di-dimethyldioleyl ammonium phytate, as described inUS. application 783, 187, filed December 29, 1958, now abandoned,tetraisoamyl ammonium picrate and the like, and combinations thereof.Other antistatic additives include lecithin, alkaloids, amines such asbetaine alkanol amines, asphaltenes, alkali and alkaline earth petroleumsulfonates, amine and ammonium and quaternary ammonium salts of dialkylphosphoric acid, P 8 treated hydrocarbons such as the barium salt of P 5treated polyisobutylene and the like, and other additives such as thosedescribed in US. application 695,469, filed November 8, 1957, nowabandoned, and in US. Patents 2,951,751, issued September 6, 1960, and2,974,027, issued March 7, 1961. As is apparent, the applicantsinvention is not dependent upon the particular additive compound, butmay be beneficially employed with all additives that enhance electricalconductivity and which are subject to separation into two fractions,e.g., a dialyzable and undialyzable fraction.

Normally, the colloidal or undialyzable fractions of these antistaticadditives, for example, the metallic complexes, range from 1 to about60% by weight of the total complex, but may be as high as 99.5 wt.percent and as low as 0.5 wt. percent for nonmetallic additives. Thecolloidal fraction is more effective than the total complex employed atsimilar concentration levels and many be from to 100 times moreeffective than the noncolloidal or dialyzable fraction. This representsa significant unexpected improvement in electrical conductivity.

The organic liquids in which the antistatic additives are employed topromote electrical conductivity and which may also form the dispersionmedium of the colloidal systems or be the dialyzing liquid are organicliquids and preferably hydrocarbon oils boiling in the range between 75F. and 750 F. Examples of organic liquids are aliphatic hydrocarbons ormixtures thereof, such as hexane, heptane, isooctane, petroleum naphtha,andgasoline; aromatic hydrocarbons or mixtures thereof, such as benzene,toluene and the xylenes; cycloaliphatic hydrocarbons, such as deealin;mixtures of various aliphatic, cycloaliphatic and aromatic hydrocarbons;halog enated hydrocarbons or mixtures thereof, such as chloroform,carbon tetrachloride, trichloroethylene, bromobenzene, andtetrachloroethylene and ethers, such as diethyl ether and dioxane; andother liquids such as carbon disulfide, synthetic ester lubricatingoils, natural oils derived from animal, vegetable or marine sources.

The process is particularly useful where the recovered active fractionis to be incorporated in gasoline, aviation turbojet fuel, kerosene,diesel fuel, lubricating oils, greases, asphalt, waxes, cutting oils,fuel oils and other petroleum distillate fuels and products. Gasolineinclude both motor gasolines and aviation gasolines such as thosedefined by AST-M Specifications D9l057-T and D-439-58T. Aviationturbojet fuels are described in length in US. Military SpecificationsMIL-F-25524A, MIL-F-5624D, MILF25558B, and MILF25656(1), and in ASTMSpecifications for Aviation Turbine Fuels D-1655-59T. Diesel fuels andfuel oils as referred to in connection with the invention are defined inASTM Specifications D97559T and D39648T.

The treatment of the liquid colloidal system containing the antistaticadditive may be accomplished in a liquid concentrate containing a'majorportion of the additive agent, e.g., from 50 to 75 or 95 wt. percent, oron the additive without liquid diluent. The dialysis medium can be anyliquid, such as water or aqueous solution;

but organic liquids, for example, as previously described, in which theadditive material forms a dialyzable or colloidal fraction, arepreferred. Thus, the dialysis liquid may be a substituted ornonsubstituted, saturated or unsaturated normally liquid aliphatic,alicyclic, alkyl, alkylene, alkyne, aromatic, alkylaryl, an arene, suchas an alcohol, an aldehyde, an ester, a ketone, an ether, a hydrocarbonand the like or a combination of these liquids. The best liquid mediumto use will depend in part on the additive to be employed, the amount ofcolloidal fraction formed in a particular liquid, the nature of theliquid, the end use of the additive, and other factors within selectionof the chemist. It has been found that it is best to employ as theliquid dialysis medium a similar liquid in which the undialyzablefraction is subsequently employed. For example, where the process isemployed to concentrate an additive for subsequent incorporation into asubstantially liquid parafiinic jet fuel like LIP-4, it is preferred toemploy a dialyzing liquid of similar chemical structure andcharacteristics, such as a hydrocarbon oil like isooctane or JP-4. Thus,for employment of the additives in distillate petroleum products, aliquid hydrocarbon medium should be used such as a saturated C Chydrocarbon like isooctane, hexane, heptane, or a paraffinic hydrocarbonmixture having a boiling point range of from to 450 R, such as gasoline,JP4, and the like. After dialysis or comparable treatment, the activecolloidal fraction may be incorporated directly into the desiredcombustible organic liquid or in an additive concentrate in combinationwith other additives conventionally employed in such liquids, such asrust inhibitors, antioxidants, dyes, dye stabilizers, detergents,polymeric dispersant s, surfactants, scavenging agents, antiknocks, andthe like.

The concentration of the colloidal fraction may be accomplished by anymeans which permits the separation of the colloidal fraction of theantistatic colloidal system from the noncolloidal or molecular fraction.The most common methods employed depend upon the differences indiffusion characteristics between the larger colloidal particles whichare retained by a semipermeable membrane and those molecular orcrystalloid fractions which readily diffuse through the membrane. Thus,separation by dialysis is the most common and simplest method with therate and method of dialysis being dependent on many factors, such as thearea of the dialyzer, the membrane employed, the size of the pores, thetemperature, the electrical charges, relative concentrations of thesolution on either side of the membrane, and the like.

In the separation of fractions by diffusion methods, semipermeablemembranes in the form of sacks, sausage skins, seamless thimbles, or thelike may be employed. Suitable membranes includes various natural animaland artificial membranes which contain pores so that dissolved moleculesand ions can pass through, but which retain the colloidal fractions.Some suitable mem branes include cellophane, collodion membranes,natural, synthetic and latex type rubbers, cellulose acetate, paper,plastic, and the like. Membrane selection must. also be based onconsiderations as to the effect of the dialysis liquid on the membrane.For example, an aromatic dialysis liquid like toluene with a, rubbermembrane might initially be suitable, but in time changes in the poresize of the membrane beyond the critical limits desired might occur.Ordinarily, dialysis is a slow process, but the use of electrodialysishas facilitated the rate of separation. In this method, the colloidalsolution is placed between the two dialyzing membranes with water orother liquid compartments containing electrodes on each side. Therapidremoval of charged particles is then accelerated by the use of anapplied voltage, e.g.,

of from about 50 to 300 volts.

Separations may, also be accomplished by ultrafiltragrained tion meanswhereby the colloidal solution or system is filtered through asemipermeable membrane of specially treated filter paper or the likewith the passage of the liquid dispersion medium accelerated by pressureor suction. Additional means include the use of ultracentrifuge methodswhereby high speed, i.e., above 30,000 r.p.m., Svedberg ultracentrifugesallow the separation of the colloidal and noncolloidal fractions of acolloidal system.

Other means of treating the antistatic colloidal system to increase theamount of the active colloidal fraction include methods whereby one ofthe fractions is removed by precipitation, flocculation, or coagulation;the use of ion exchange resins; molecular sieves; sonic methods; and thelike. Due to economy and simplicity, dialyzing means employingsemipermeable membranes are preferred.

The exact nature and objects of the invention may be more fullyunderstood by reference to the following examples.

EXAMPLE 1 Complexes were prepared by reacting chromic acetate with oleicacid and dodecyl phenol sulfide directly or in the presence of solventsat temperatures between about 180 F. and about 300 F. as follows:

A. A solution of 10.0 g. (0.018 mole) of dodecylphenol sulfide and 0.37g. (0.0015 mole) of chromic acetate in 200 ml. of absolute ethanol washeated on a steam bath until all the alcohol was removed. A clear, dark,reddish-green viscous product was obtained.

B. A mixture of 10.0 g. (0.018 mole) of dodecylphenol sulfide and 0.37g. (0.0015 mole) of chrornic acetate was stirred on a steam bath for 12hours during which time the mixture gradually became clear. A dark,reddish-green viscous product was obtained.

Complexes were prepared by reacting chromic acetate and oleic acid asfollows:

C. A solution of 2.47 grams of chromic acetate (0.01 mole) in 50 ml. ofethanol was added to a solution of 16.9 grams of oleic acid (0.06 mole)in 50 ml. of ethanol. The resulting solution was evaporated to drynesson the steam bath, whereupon 17.9 grams of a reddish-green, tacky solidwere obtained.

EXAMPLE 2 The metallic antistatic complexes of Example 1 were thendialyzed to separate the colloidal and noncolloidal fractions of thecomplexes. Dialysis was accomplished by placing the antistatic metalcomplex in a finger-shaped, rubber, semipermeable membrane suspended inisooctane in a Soxhlet extractor and slowly refluxing to continuouslyextract the noncolloidal fraction I which passes through the membrane.The colloidal, or undialyzable, fraction II is retained within therubber membrane finger. These fractions were then incorporated alongwith the total complex in various samples of JP-4 fuel and theelectrical conductivity of the fuel determined to test theeifec'tiveness of the additive fractions in comparison with the totalfraction. In this method the dialysisliquid is i-sooctane, Whiletheadditive comprising a colloidal and noncolloidal fraction is beingemployed in concentrate form.

The fuel employed in carrying out these tests was representative of theaviation turbojet fuel classified as JP-4 fuel and defined by US.Military Specification MIL-F-5624D. It had an API gravity of 48.7 aReid, vapor pressure of about 2.5 pounds per square inch and a boilingrange between about 100 and about 500 F.

I Weight Specific Ratio, v Composition percent of Oonduc- (base) toOriginal tivity, 11 cr (base+ Additive (mho/cm additive) Base .TP-4 None0. 04

Base JP-4:

Plus 0.002 wt. percent Additive A 100 5. 9 118 Plus 0.002 wt. percentAdditive A, Fraction I 92 1.1 28 Plus 0.002 wt. percent Additive A,Fraction II 8 140 3, 500 Plus 0.002 wt. percent Additive B a. 100 5. 9118 Plus 0.002 wt. percent Additive B, Fraction I 74 0.2 5 Plus 0.002wt. percent Additive B, Fraction II 26 89 2, 235 .Plus 0.002 Wt. percentAdditive O 100 45.3 1,510 Plus 0.002 wt. percent Additive 0, Fraction I45 0.3 10 Plus 0.002 wt. percent Additive 0, Fraction II 53 287 9, 560

The tests werecarried out by applying a fixed, directcurrent voltageacross a standard conductivity cell'containing the sample to be tested.-A standardhigh-resistance element was connected in series with the cell1 and the current which flowed inthe circuit during the test wascomputed by measuring the voltage across the resistance element andapplyingrO hmsvlaw. The resistance of the sample, the specificresistance and the specific conductivity were in turn computed. Theresults of these tests are shown below for the base fuel and for thesamples of the base fuel containing the various additives.

Table I EFFECT OF DIALYSIS UPON THE SPECIFIC CONDUCTIVITY OF METALLICADDITIVES IN JP-4 Table II THE EFFECT OF ADDITIVE CONCENTRATION UPON THECONDUCTIVITY OF JP-4 Specific Ratio, Condue- 0' (Base) to tivity, o", a(Base-{- mholoc r mx Additive) Concentration, Wt. Percent of Additive A,Fraction II None 0. O4 5. 0 21 530 sec 9, 000

The foregoing demonstrates that the colloidal fraction obtained bydialysis is extremely effective over a wide range of concentrations andyields conductivity results approximately proportional to the additiveconcentration employed.

EXAMPLE 4 v A further demonstration of the efficacy of the presentprocess and its ability to concentratethe most effective and the activeportion of both metallic and nonmetallic antistatic additives is shownby thefoll'owing data of Table III. I An aLkyl C -C hydroxyl aromaticsulfide, for example, an alkyl phenol sulfide, and a tetraaliphatic C Cquaternary ammonium phyta-te Were'dialyzed'and tested.

phenol sulfide were dialyzed by placing these compounds in a naturalrubber, finger-type membrane in a Soxhlet extraction apparatus andemploying isooctane as the continuous liquid dialysis medium. Theresults of conductivity measurements were determined as before with thefollowing results. Fraction I represents the dialyzed fraction, whileFraction II represents the undialyzable fraction retained by themembrane.

Table III EFFECT OF DIALYSIS UPON THE SPECIFIC CONDUC- TIVITY OFNONNIETALLIO ADDITIVES IN JI-4 The foregoing data indicate the broadvalue of the instant process to all antistatic additives. For example,dodecyl phenol sulfide was demonstrated to be a wholly ineffectiveadditive to promote electrical conductivity. Upon. concentration of theactive colloidal or undialyzable fraction of this additive, thisfraction was very effective in en-- hancing the specific conductivity ofJP-4. The two di-- verse nonmetallic additives, as shown above, allowsig-- nificant and unexpected enhancement of the electrical conductivitywhen Fraction II was incorporated into JP-4. It; should be noted thatthe effectiveness of the undialyzed fraction was not dependent on theamount dialyzed since in one case Fraction II constituted 0.5 wt.percent, while in the other Fraction II constituted 98.6 wt. percent ofthe total additive dialyzed.

EXAMPLE 5 tivity of the fuel more than a comparative concentration.

of the total additive.

EXAMPLE 6 An antistatic additive having unexpected electricalconductivity characteristics is obtained by incorporating about 10 to 50wt. percent of chromium octyl salicylate in hexane to form a colloidalsystem, and subsequently dialysingsaid colloid-containing solutionemploying a cellulose containing, semipermeable membrane with hexane asthe dialysis liquid. The solution fraction retained by the membrane whenincorporated in carbon disulfide at a concentration level of about 0.01wt. percent enhances the electrical conductivity of the fuel more thanthe comparative concentration of the total additive.

It is, of course, recognized and within the scope of the invention thatthe concentrated or active colloidal fractions obtained by theapplicants process may be subsequently employed alone or in volatileorganic and in aqueous solutions to treat the surface of various solidarticles which have a tendency to accumulate, generate, orstore staticcharges. Thus, for example, the active colloidal fraction oftetraaliphatic ammonium pliytates such as di-dimethyldioleyh ammoniumphytate may be utilized to treat the surfaces of articles such asvinyl-containing resins, synthetic textile fibers and yarns or filmscontain ing polyester resins, vinyl chloride, polyethylene, vinylidinechloride, cellulose, natural animal or vegetable fiberslike wool,cotton, natural and synthetic rubber and the like, and combinationsthereof. Treatment of these surfaces to aid in dissipating theelectrical charge that accumulates by frictional contact or movement maybe accomplished by painting, spraying, dipping, impregnating, immersing,coating or otherwise placing the active fraction on the surface to beprotected.

In summary, the applicants have discovered that the separation of thecolloidal fraction of an antistatic additive produces a fraction whichhas enhanced ability to promote electrical conductivity. The instantdiscovery is not dependent upon the particular type of additive or uponthe separating means employed, but rather on the discovery that acertain fraction, when separated from the total additive, has unexpectedantistatic effectiveness.

What is claimed is:

l. A process for concentrating the active fraction of antistaticadditives which additives form colloidal and noncolloidal fractions,said process comprising dialyzing said antistatic additive in order toeffect at least partial separation of the noncolloidal fraction and thenrecovering the concentrated colloidal fraction, said concentratedfraction having an enhanced ability to promote electrical conductivity.

2. A highly effective antistatic composition consisting essentially ofthe concentrated colloidal fraction of an antistatic additive producedby the process of claim 1.

3. A highly effective antistatic composition consisting essentially ofthe concentrated colloidal fraction of an antistatic additive producedby the process of claim 1 wherein said antistatic additive is thereaction product of dodecylphenol sulfide and chromic acetate.

4. A highly effective antistatic composition consisting essentially of aconcentrated colloidal fraction of an antistatic additive produced bythe process of claim 1 wherein said antistatic additive is a chromiumsalicylate.

5. A highly effective antistatic composition consisting essentially ofthe concentrated colloidal fraction of an antistatic additive producedby the process of claim 1 wherein said antistatic additive is aquaternary ammonium compound.

6. A process as defined in claim 1 wherein said colloidal fraction isconcentrated by dialysis means.

7. A process as defined by claim 1 wherein said colloidal fraction isconcentrated by electro dialysis means.

8. A process as defined by claim 1 wherein said colloidal fraction iscomposed of colloidal particles having average diameters of less than 1micron.

9. A hydrocarbon turbojet fuel boiling in the range of from F. to 750 F.to which has been added a minor amount sufiicent to promote theelectrical conductivity of said fuel of a concentrated, colloidalfraction of a metallic antistatic additive produced by the process ofclaim 1.

10. A combustible organic liquid boiling in the range of from 75 to 750F, said liquid containing a minor amount suiiicient to increase theelectrical conductivity of said liquid to a value greater than l 10 mhosper centimeter of a concentrated colloidal fraction prepared byselecting an antistatic additive which additive comprises acolloidalfraction and a noncolloidal fraction; dialyzing said antistatic additivein order to effect at least partial separation of the noncolloidalfraction; and r covering the concentrated colloidal fraction.

11. A process for improvin the electrical conductivity of a combustibleorganic liquid boiling in the range of from 75 to 750 F., said processcomprising selecting an antistatic additive which additivecomprises acolloidal fraction and a noncolloidal fraction; dialyzing said'additivein order to effect at least partial separation of the noncolloidalfraction; recovering the concentrated colloidal fraction; addingsaid'colloidal concentrated fraction to said combustible organic liquidin a minor amount sufficient to increase the electrical conductivity ofsaid liquid to a value greater than l lO- mhos per centimeter;

12. A process for concentrating the active fraction of an antistaticadditive, which process comprises dialyzing said antistatic additiveemploying an organic liquid as the dialysis medium and recovering theconcentrated undialyzed fraction, which fraction has an enhanced abilityto promote electrical conductivity.

13. A process as defined by claim 12 wherein the organic liquid is ahydrocarbon boiling in the range between 75 and 750 F.

14. A process as defined by claim 12 wherein the said antistaticadditive is a chromium-containing compound.

15. A process as defined by claim 12 wherein the said antistaticadditive is a quaternary ammonium compound.

16. A process as defined by claim 12 wherein the said antistaticadditive is an alkyl hydroxy aromatic sulfide.

1 i) 17. A process as defined by claim 12 wherein said dialy- 1,680,349Urbain Aug. 14, 1928 2,375,957 Stamberger May 15, 1945 2,648,636 Elliset a1 Aug. 11, 1953 2,758,966 Raymond Aug. 14, 1956 2,951,751 McDermottSept. 6, 1960 2,974,027 Di Piazza May 7, 1961 FOREIGN PATENTS 503,833Canada June 22, 1954

10. A COMBUSTIBLE ORGANIC LIQUID BOILING IN THE RANGE OF FROM 75* TO750*F., SAID LIQUID CONTAINING A MINOR AMOUNT SUFFICIENT TO INCREASE THEELECTRICAL CONDUCTIVITY OF SAID LIQUID TO A VALUE GREATER THAN 1X10**-12MHOS PER CENTIMETER OF A CONCENTRATED COLLOIDAL FRACTION PREPARED BYSELECTED AN ANTISTATIC ADDITIVE WHICH ADDITIVE COMPRISES A COLLOIDALFRACTION AND A NONCOLLOIDAL FRACTION; DIALYZING SAID ANTISTATIC ADDITIVEIN ORDER TO EFFECT AT LEAST PARTIAL SEPARATION OF THE NONCOLLOIDALFRACTION; AND RECOVERING THE CONCENTRATED COLLOIDAL FRACTION.